VP of People at Gorilla | In the pursuit of employee significance | Leadership & Career Coach | Illustrator | Corporate Hippy - views expressed here are my own

I’m a tech executive who believes the future belongs to companies that combine AI capability with human intelligence.

Not AI as a silver bullet.
Not people strategy as soft culture work.
Not simplistic “do more, faster” productivity narratives.
But practical systems that help organisations make better decisions as they scale.

I’ve spent my career building and operating those systems across people, performance, operating models, and now AI. 

The work only matters if it shows up in reality; how leaders lead, how teams decide, and how companies change without losing trust.

Most recently, I led the global People function at a Series B energy tech company and co-led our early AI rollout across governance, ethics, enablement, tooling, and experimentation. 

Alongside this, I work with founders, executives, and investors as a fractional leader and advisor. I help organisations roll out AI responsibly, navigate change, and build people systems that compound growth rather than create drag.

If you’re a founder, COO, CPO or leader trying to:
- adopt AI without breaking trust or momentum
- lead change without drowning managers in process
- scale people and operating systems that actually work in the real world.

I write and speak for you.

Things I write about:

- Practical AI adoption without hype or harm
- Where human judgment still matters in everyday AI decisions
- Leading change that creates clarity and engagement, not chaos
- People systems that support growth instead of getting in the way
- Why culture breaks during scale-ups, and how to fix it

Vanessa Monsequeira

It's been a big week, folks

I'm hopping on a plane to Australia for a workation. 

On the agenda:
🌞 Surf - Sun - Seafood.
☕ A proper flat white (finally).
💜 Laughs with family and friends.

Also on the agenda:

Customer calls with Europe from my laptop .. beachside. 

Coffee catch-ups and lunches with Aussie legends. Megan Trotter Matt McFarlane Mark Lewis Mohit Midha Careen Matthews Adam Axon 

to have lots of conversations about AI, People Experience and HR Tech. 

Basically defrosting before tulip season drags me back.

See you on the flip side.

Vanessa Monsequeira - चित्रलेखा

AI Transformation and Change Leadership | Fractional VP People | Building Work as a Product | Corporate Hippy

A woman with dark curly hair and gold-rimmed glasses grins broadly at the camera, holding up an Australian passport. She's wearing a colourful plaid scarf and a red jacket, photographed in an airport terminal.

2 months ago, I had to decide to stay in-house or bet on myself and go solo.

I knew which direction pulled at me.

But I was about to play it safe: positioning myself in a category that felt comfortable, familiar and small.

I told myself I didn't have the right to play in AI.

Even though I'd led AI adoption in my last organisation.

Even though our VC asked me to present best practices and pitfalls to their portfolio companies.

The doubts were loud:
↳ “I'm not technical enough”
↳ “What about the financial risks?”
↳ “Who am I to claim this space?”
↳ “What if I am no good?”

Then I met Frans van Loef in January. 

A busy executive coach, author and former CEO. The kind of person whose calendar you don't expect to make it onto twice.

We had a mentoring conversation over a year ago.

But when we sat down at the same café, same table, it felt like no time had passed.

Like catching up with an old friend who wasn't going to let me shrink. And someone who could show me what it actually looked like to back myself.

He didn't let me get away with playing small.

Frans didn't give me a pep talk. He held up a mirror.

Not just to the last 15 months of AI work, but to 15 years of leadership, change, transformation, tech and business consulting.

The pattern was right there. I'd been doing this work all along, I just hadn't claimed it.

That conversation shifted something.

I stopped waiting for permission and started building.
(more on this every week)

Last week, I launched my business.

I help tech leaders close the gap between AI ambition and AI outcomes, without burning out their managers or losing top talent.

Since then, I've had multiple enquiries and calls.

That's what happens when someone helps you see what you've been too close to see yourself.

Building a business will never be easy.

But if there's a "shortcut", it's having someone who can reflect your capability back to you when self-doubt is doing the talking.

Then it comes down to backing yourself. FULLY.

Frans, thank you for being in my corner!


PS. I’m about to launch my newsletter on How AI is rewiring thinking, leadership, and the workforce. Get it for free: https://lnkd.in/eh_aYrzw

Close-up selfie of two people smiling warmly at the camera indoors. On the left, a man with short light brown hair and blue eyes wears a navy collared shirt. On the right, a woman with shoulder-length dark curly hair wears a light knit top, gold necklace, and colorful earrings. They are standing close together in a cozy space with exposed brick and soft natural light in the background.

Anthropic dropped their AI fluency report this week.

Two findings made me curious and hungry:

1. AI Fluency is strongly linked to iteration and refinement, not just output volume.

2. When creating outputs (e.g. documents, code), users get more directive but less evaluative.

AI is making us better but only if we use it to augment our thinking, not delegate, deliver and forget. 

I believe the answer isn't to stop using AI to create outputs.

It's to use it with critical thinking:
↳ Structure Problem Solving
↳ Analysis and Critique
↳ Decision Making 

The problem is that critical thinking is rarely taught in schools, universities, or businesses.

So we're handing people a powerful tool with no framework for how to actually think with it.

That's why I built the The Critical Thinking Sandwich:

Your thinking is the bread: Thick, sturdy, holding everything together.

The filling (meat or veg) is where the real work happens: The iteration, the critique, the refinement.

AI is the cheese: Essential, delicious, sticks things together, but never the main event.

AI is the cheese but it doesn't make the sandwich.

Your thinking does.


#criticalthinking #AI #cognitivedebt

"How to stay sharp when AI does the work" showing The Critical Thinking Sandwich — a five-layer framework for using AI without losing your edge.
Layer 1 (orange, thick): Critical Forethought. Frame the problem yourself before you prompt.
Layer 2 (yellow, thin): AI Output v1. Raw material. Not the answer.
Layer 3 (green, thick): Critical Analysis. You interrogate first, then ask AI to challenge it from multiple angles.
Layer 4 (yellow, thin): AI Output v2+. Refined and pressure tested.
Layer 5 (orange, thick): Critical Readiness. Can you defend this without AI? If not, go back into the filling.
Footer: "AI is the cheese. It doesn't make the sandwich."

IT teams are about to become everyone's problem.

Most leaders haven't realised it yet.

At a hackathon last month, Debora Gallo shared an example that I haven't stopped thinking about. 

People teams are starting to build their own tools. 

Personalised, scrappy and iterative is exactly what the business needs. 

And IT's response was awesome, but we can't maintain that. 

I've seen this movie before. 

Years ago I was brought in as a tech consultant because a company's manufacturing engineering team had started building their own systems rather than waiting in the IT queue. 

They would "dev all the way to core systems" and then throw it over the fence to IT. 

IT was getting frustrated: 
→ Those systems needed to talk to central infrastructure. 
→ They needed someone to maintain them post development. 
→ They needed security sign-off. 

But nobody had planned for it because they went around IT.

They thought IT was too slow and always said no.  

And the whole thing became an expensive, political mess to untangle. 

That was considered an edge case back then. 

"Shadow IT" was the awkward anomaly everyone quietly complained about. In the age of vibe-coding, it becomes the default. 

And the People team won't be the only ones building. 

Finance, Ops, Marketing, Sales and any function with a problem and a bit of curiosity can now ship something. 

That's genuinely exciting! 

But it's also a structural time bomb if no one is asking the harder questions. 

What leaders need to start doing: 

1️⃣ Map your org design for a world where every function can build, not just request. 

2️⃣ Set the rules now: maintenance, governance and security can't be an afterthought when every team is shipping. 

3️⃣ Audit your future roles and skills. Agentic AI and vibe-coding are rewriting what every job actually requires. 

Keen to hear if you've been doing or observing any of the above. 

#aiadoption #orgdesign #futureroles

Black background with large white serif text reading "In organizations when everyone is vibe-coding......." with the words "vibe-coding" highlighted in purple, followed by "Who will maintain our apps?" with the word "maintain" highlighted in coral orange. Vanessa Monsequeira and Intentional AI Adoption appear in small text at the bottom left and right corners.

Are you team OpenAI or Anthropic?

For me, it's Anthropic for the win. 

I love:
🧡 Claude Chat
🧡 Claude Cowork
🧡 Claude Code (still WIP)

I appreciate a tool that doesn't optimise for dopamine.

No endless suggestions designed to keep you hooked.
(Worth a listen: Lenny's Podcast with Edwin Chen, CEO of Surge)

I support co-founders who:

a) Give away 80% of their personal wealth
b) Don't donate $25M to oppressive political regimes

I support a CEO (Dario Amodei) who writes real thought leadership:

→ The Adolescence of Technology
→ Machines of Loving Grace

Are any of these founders perfect? No
Is the wealth amassed insane? Yes

But the AI bubble isn't bursting anytime soon.

And what that means for employees is non-negotiable:
Upskill on tooling, critical thinking, and ethics.

In my opinion,  🧡 Anthropic for the win on all three.

Video credit: Reuters at AI Summit India

#aiwars #techbrodisputes #AI

Have you every attended a 'conference' that changes the way you think, learn and experiment?

For me that's been PX experiences by SapienX.

Every year I learn things from fellow speakers and peers that keeps me coming back. 

Every single time I've been able to put what I've learned into action immediately.

Key highlights:

🗓️ 2024 - London

➟ How to launch people products using best practices from marketing 
➟ UX to PX applications and north star and meaningful metrics 
➟ Deep dives into service design and the double diamond, and interactive icebreakers I still steal to this day. 
➟ Everyone comes to the game of work with the same set of cards but a different set of rules from past workplaces... and we expect everyone to play the same game 

🗓️ 2025 - London and Amsterdam

➟ PX in action for performance design 
➟ PX and service design deeper dives 
➟ Practical applications of agile for people teams 
➟ The culture card game and a touch of wizardry 
➟ Experiment Design canvas - integrating all our learnings into action 
➟ Purpose at work interactive session and preview of Jessica Zwaan's new book 
➟ The future of HR turning into the future of design of work, workforce, and workflows 


🗓️ 2026 What will we see next? 

Join us at PX Live to find out.

It's going to be a cracking line-up:

Alicia Grimes
Dart Lindsley
Glenn Martin
Chris Metcalfe
Luke O'Mahoney
Thomas Forstner
JooBee Yeow, PhD (OOO)
and me Vanessa Monsequeira - चित्रलेखा

If you're: 
👉🏽 A Head of People trying to drive real impact 
👉🏽 A PX leader building capability beyond admin 
👉🏽 Someone who believes the People function can be more strategic

come join us for the fun, to learn, and to be part of the movement to redesign the future of HR and work.

It's on March 20 and it's limited to 100 practitioners.

Discount code - VANESSA-10

#peopleexperience #pxlive

Promotional banner for PX Live London featuring a diverse audience smiling and seated at a live event. Overlaid text reads: “Work is broken. Product can fix it.” Event details: “PX Live — London | March 20th.” “Limited tickets available” appears alongside a QR code. Supported by hownow, Humaans, and huggg. Sapien logo in the top left corner.

Kyle Thomas

Went from cubicle data entry to Uber Employee 250 & Startup Exec | Helping you land your career-accelerating role in less than 90 days | Founder & CEO of UpEmployment Accelerator

When it comes to startup job seeking everyone wants to be an early employee at a unicorn 🦄 & earn millions 💸.

But what's the secret to landing those opportunities? 

Here's a hint...

They don't come from the "traditional job search".

When I was job seeking I had no idea what I was doing, but with experience and research, I found ways to stack the deck in your favor.

That's what led me to land a job as Uber's 250th employee. 

After Uber, it's what led me to a VP role with a $100k salary increase at a Y-Combinator startup.

That's why I built Early.

Do you have amazing experience & want to take the next step to accelerate your career in a startup, but not sure where to start?

I wished that someone had a playbook for how to do that. 

It didn't exist, so I created it.

The Early Accelerator gives highly talented job seekers a complete playbook for how to land your next dream role plus accountability & a community to guide you along the way.

The program is designed to allow you to:
- 10x your job hunt efficiency
- Know where you want to go
- Build your personal brand
- Know the salary and equity you command
- Create a system to generate connections & opportunities
- Generate 100x more warm network connections
- Leverage repeatable frameworks
- Get in a peak performance state
- Create unwavering confidence
- Get to your dream role

Despite the challenging job market, we have seen incredible results.
↳ Average job searches lasting ~3 months (90 days vs US avg of 5 months).
↳ >$200k in salary increases.
↳ >$800k in equity increases.
↳ Total compensation increases of over $1M.
↳ Advancements from Manager to Department Head.
↳ Major career jumps from VP to the C-Suite.

I formalized the proven system into an easy-to-execute framework that anyone can use to land their dream job.

My mission is to help millions live extraordinary lives by accessing opportunities that change their careers forever.

You deserve to work in a job that lights you up, pays you what you are worth, and accelerates you toward your vision of your dream future.

Let's go get you that job!

So, D.M 📩 me here or email me at kyle@BeEarly.com today so we can accelerate your startup career the right way.

Stop wasting time applying to every company where you meet the minimum qualifications and learn our proven way to land your dream job!

P.S. If you're a startup job seeker looking to cut your job search in half, outperform over 95% of other candidates, and land a top startup job, click the link in my Featured Section and apply today!

Founder

I take groups of people from A to Z in their job search so they can land their dream job without applying online.

These methods took me from cubicle data entry to a job as Uber employee 250 and from unemployed to startup executive. I'm not special, I can teach you to do the same!

Everyone's applying to the same 20 companies.

These 35 startups can't hire fast enough.

You want to join a team that's growing, not shrinking.

But which startups are growing the most?

I took the last 90-day hiring numbers for...
• Series A, B, and C startups 
• with HQ offices in major markets across the US 
• and funding in the last 12 months

These are the top 5 in each city that hired the most and are actively hiring today.

Even if you're not located in these cities, Many of the companies are hiring outside of HQ and for remote roles.

𝗔𝗨𝗦𝗧𝗜𝗡
SEON (31 open roles)
Allen Control Systems (39 open roles)
Aalo Atomics (16 open roles)
Arintra (5 open roles)
Harbor Health (45 open roles)

𝗕𝗢𝗦𝗧𝗢𝗡
Ledgebrook (14 open roles)
Kodex (3 open roles)
OneLayer (2 open roles)
CollegeVine (10 open roles)
Blue Water Autonomy Inc. (20 open roles)

𝗖𝗛𝗜𝗖𝗔𝗚𝗢
Nerdio (22 open roles)
Toro TMS (2 open roles)
Coinflow (11 open roles)
MUSH (3 open roles)
HOPPR (7 open roles)

𝗠𝗜𝗔𝗠𝗜
Félix (89 open roles)
Flow (34 open roles)
Boom (2 open roles)
FANBASIS (1 open role)
Guardz (14 open roles)

𝗡𝗘𝗪 𝗬𝗢𝗥𝗞
Nourish (108 open roles)
Arch (28 open roles)
Dash0 (25 open roles)
Tennr (28 open roles)
incident.io (29 open roles)

𝗦𝗔𝗡 𝗙𝗥𝗔𝗡𝗖𝗜𝗦𝗖𝗢
Substack (23 open roles)
Mercury (58 open roles)
Eve (26 open roles)
LangChain (67 open roles)
Peregrine (81 open roles)

𝗦𝗘𝗔𝗧𝗧𝗟𝗘
XBOW (49 open roles)
Supio (11 open roles)
MIND (12 open roles)
Augmodo (1 open role)
Aurelian (11 open roles)

Go get that job and build something awesome 💪
_________________________________________________

For more lists & job search tips, follow me, Kyle Thomas.

♻️ Share this to help startup job seekers find a new role.

💬 Want help in your startup job search? Check out the link in my profile to see how Early can help.

I Teach Ambitious Startup Job Seekers How To Land Career-Accelerating Roles at World-Changing Startups | “De-Risk” the Search w/ Proven Methods & Investor-Grade Data | Apply to our Startup Job Search Accelerator Below

LA is the #5 startup ecosystem in the US.

Most job seekers treat it like an afterthought.

After my post about the fastest-hiring US startups, I got a bunch of DM's asking for other lists.

One person asked me to do LA, so...

I took the last 90-day hiring numbers for...
• Series A, B, and C startups 
• with HQ offices in LA 
• and funding in the last 12 months

𝗧𝗵𝗲𝘀𝗲 𝟭𝟬 𝘀𝘁𝗮𝗿𝘁𝘂𝗽𝘀 𝘄𝗶𝘁𝗵 𝗛𝗤 𝗶𝗻 𝗟𝗔 𝗿𝗮𝗶𝘀𝗲𝗱 𝘁𝗵𝗲𝗶𝗿 𝗹𝗮𝘀𝘁 𝗿𝗼𝘂𝗻𝗱 𝗶𝗻 𝘁𝗵𝗲 𝗹𝗮𝘀𝘁 𝘆𝗲𝗮𝗿 & 𝗵𝗶𝗿𝗲𝗱 𝘁𝗵𝗲 𝗺𝗼𝘀𝘁 𝗶𝗻 𝘁𝗵𝗲 𝗹𝗮𝘀𝘁 𝟵𝟬 𝗱𝗮𝘆𝘀 👇

 1. Akido Labs (51 open roles)
 2. Neros Technologies (41 open roles)
 3. Dose (2 open roles)
 4. Reflect Orbital (23 open roles)
 5. Atticus (14 remote open roles)
 6. Jump (2 remote open roles)
 7. Axle Health (6 open roles)
 8. Karman Industries (8 open roles)
 9. Quilter (4 open roles)
10. SimpleClosure (11 open roles)

𝗛𝗲𝗿𝗲 𝗮𝗿𝗲 𝘁𝗵𝗲 𝟭𝟬 𝘀𝘁𝗮𝗿𝘁𝘂𝗽𝘀 𝘄𝗶𝘁𝗵 𝗛𝗤 𝗶𝗻 𝗟𝗔 𝘄𝗵𝗼 𝗵𝗶𝗿𝗲𝗱 𝘁𝗵𝗲 𝗺𝗼𝘀𝘁 𝗶𝗻 𝘁𝗵𝗲 𝗹𝗮𝘀𝘁 𝟵𝟬 𝗱𝗮𝘆𝘀 𝗿𝗲𝗴𝗮𝗿𝗱𝗹𝗲𝘀𝘀 𝗼𝗳 𝗹𝗮𝘀𝘁 𝗳𝘂𝗻𝗱𝗶𝗻𝗴 𝗱𝗮𝘁𝗲 👇

 1. Rula (22 open roles)
 2. Function Health (30 remote open roles)
 3. K2 Space Corporation (122 open roles)
 4. Thrive Market (20 open roles)
 5. CloudKitchens (56 open roles)
 6. hello82 (7 open roles)
 7. GrayMatter Robotics (12 open roles)
 8. Third Way Health (23 open roles)
 9. Tower 28 Beauty, Inc. (6 open roles)
10. Cider (12 open roles)

If you're not LA based, there are also remote roles and roles in other cities at the companies on this list.

Go get that job and build something awesome 💪

Also...

Let me know in the comments or shoot me a DM if you want to see a future post on a specific industry, location, size, or stage of company.

I want to give you exposure to what's out there.

Shoutout to Harmonic for the data.
_________________________________________________

For more lists & job search tips, follow me, Kyle Thomas.

♻️ Share this to help startup job seekers find a new role.

💬 Want help in your startup job search? Check out the link in my profile to see how Early can help.

>200 FinTech companies have raised money in 2026. Here are 30 w/ top investors & open roles 👇

𝗛𝗲𝗿𝗲’𝘀 𝘁𝗵𝗲 𝘀𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲:
• Company Name
• 🦄 = Valuation > $1 B
• 🏆 = > 90 % PitchBook success probability
• What they do
• Recent round stage, round size
• Position locations
• Openings by function

1. Rogo 🏆
AI finance analytics
Series C, $75M
New York City, London, Singapore, Remote
43 Openings
Sales (13) • Engineering (5) • Security (4) • Strategic Opportunities (6) • Product/Design (5) • Talent (3) • Finance (2) • Marketing (2) • Operations (1) • Legal (1)

2. WithCoverage 🏆
AI insurance brokerage replacement
Series B, $42M
New York City, Austin, San Francisco, Chicago, Philadelphia, Salt Lake City, Remote
26 Openings
BD/Sales/Growth (11) • Engineering (5) • Product (1) • Risk (3) • Marketing (1) • Recruiting (1) • Legal (2) • Operations (2)

3. Bretton AI 🏆
Financial crime compliance AI
Series B, $75M
San Francisco, Remote
8 Openings
Business (3) • Engineering (5)

4. SPRX (Onshore)🏆
R&D tax credit automation
Series B, $31M
New York City, Houston, Los Angeles
12 Openings
Client Success (2) • Engineering (2) • Operations (1) • Sales (7)

5. Relay https://lnkd.in/eyT6tHuc 🏆
Cross-chain bridging protocol
Series B, $17M
Denver, Florianópolis, Brazil, Philadelphia, Lisbon, Remote
5 Openings
Accounting • Growth Marketing (3) • Partnerships & Business Development

6. Concourse 🏆
AI corporate finance agents
Series A, $12M
New York City, Buenos Aires
9 Openings
Engineering (4) • Product (1) • GTM (4)

7. Kalshi 🦄🏆
Prediction market platform
Series E, $1B
New York City, Remote
27 Openings
Compliance (3) • Engineering (8) • Finance (4) • Growth (6) • Operations (1) • Product (3) • Talent (1)

8. Basis 🦄
AI accounting platform
Series B, $100M
New York City
15 Openings
Deployed Intelligence (2) • GTM (7) • Operations (3) • Technical (3)

9. JUSPAY 🦄
Payments tech infrastructure
Series D, $160M
Bangalore, São Paulo, Dubai
6 Openings
Engineering (2) • Legal (1) • Design (1) • Business Development & Marketing (2)

10. Monnai 
Financial data infrastructure
Series A, $12M
United States, Latin America Bangalore
6 Openings
Growth • Sales • QA • Privacy & Security • Data Science • Software Engineering

11. Rain 🦄
Non-custodial payments network
Series C, $250M
New York City, San Juan, Remote
29 Openings
Engineering (10) • Product (5) • Compliance (3) • Growth & Sales (6) • Marketing & Design (3) • Operations (2)

12. Dots 
Multi-sided payment infrastructure
Series A, $8.9M
New York City, San Francisco, Remote
4 Openings
Sales • Growth • Engineering (2)

💬 I'll share the rest of the list in the comments.

📆 Next Monday, I'll share another list. 

Comment below the kind of list you want to see 👇

Go get that job and build something awesome!
_________________________________________________

For more lists & job search tips, follow me, Kyle Thomas.

♻️ Share this to help startup job seekers find a new role.

Fresh VC funding doesn't just create engineering jobs.

Here are 34 non-eng roles not on your radar.

All of these startups closed their last round in the last 2 weeks and are actively hiring.

𝗛𝗲𝗿𝗲’𝘀 𝘁𝗵𝗲 𝘀𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲:
• Company Name
• 🦄 = Valuation > $1B
• ⭐ = Top VC Investors
• 🏆 = >90% PitchBook success probability
• Round size, round stage, # of openings
• 3 of the current top non-eng openings + location

MatX ⭐🏆 - Chips for LLMs
($500M Series B, 24 openings)
• Corporate Controller - Mountain View
• Recruiting Lead - Mountain View
• People Ops Generalist - Mountain View

SambaNova 🦄⭐🏆 - Enterprise AI computing
($350M Series E, 13 openings)
• Sr Technical Program Manager - Santa Clara
• Sr Product Manager - Austin
• Sr Product Manager (AI Cloud) - Palo Alto

UniUni ⭐🏆 - Last-mile delivery platform
($155M Series D1, 99 openings)
• BD Manager - Fontana / Brea
• Enterprise Sales Executive - Remote
• Key Account Manager - Remote

Zafran Security ⭐🏆 - Cyber risk remediation
($60M Series C, 32 openings)
• Director of Product Marketing - Remote
• Senior Marketing Operations Manager - Remote
• AVP Sales, Enterprise - Remote

Encord ⭐🏆 - Multimodal AI data
($60M Series C, 38 openings)
• Founders Associate - San Francisco
• Head of Content - London
• Growth Manager - San Francisco

growtherapy 🦄⭐🏆 - Mental healthcare marketplace
($150M Series D, 37 openings)
• Senior Product Manager, Billing Automation - New York / San Francisco / Remote
• Performance Marketing Senior Analyst - New York
• Senior Manager, People Systems & Operations - New York / San Francisco / Remote

Profound ⭐🏆 - AI search analytics
($96M Series C, 69 open roles)
• AI Strategist
• Engagement Manager
• Manager, Account Management (Mid-Market)

Confido ⭐🏆 - CPG finance automation
($24M Series A, 17 openings)
• Head of Product - New York
• Head of Finance - New York
• Founding Growth - New York

Evervault ⭐🏆 - Data security infrastructure
($25M Series B, 10 openings)
• Founding Revenue Operations - New York
• Director of Finance - London / New York
• Business Operations - Dublin / New York

Humand ⭐🏆 - HR software for digital community
($66M Series A, 21 openings)
• Senior Revenue Ops Analyst - Remote
• Head of Data - Remote
• Client onboarding leader - Remote

Nominal 🦄⭐🏆 - Hardware testing & ops platform
($155M Series B, 41 openings)
• Business Operations Generalist - New York / Los Angeles / Austin
• Business Operations (Federal Business Development) - Washington DC
• Area Director - New York / Los Angeles

Subject ⭐🏆 - K-12 digital cirriculum
($28M Series A+, 2 openings)
• VP of Finance (CFO) - Los Angeles

Go get that job and build something awesome 💪
_________________________________________________

For more lists & job search tips, follow me, Kyle Thomas.

♻️ Share this to help startup job seekers find a new role.

💬 Want help in your startup job search? Check out the link in my profile to see how Early can help.

Your work is important.

It just shouldn’t cost you your life.

Over the last 3 years I’ve focused on nothing other than my business and my kids.

(If I’m being honest, it’s been far more than 3 years)

I’d wake up, get them ready and do school drop-off and work until pick up time.

Then back to work, dinner, bedtime and repeat.

The weekends were more work, kids’ activities, and house stuff.

Then Monday came around and I was back at it again.

There was no space left in my life for hobbies, friends or free time. 

And if I’m being honest, it almost cost me everything.

My health (multiple hospitalizations).

My relationships (bent almost to breaking).

My happiness (a shell of who I used to be).

It is so easy to be obsessed with something, lose yourself in it, and lose everything outside of it as a result.

By all means, be passionate about what you’re doing (in this case looking for your next role at a startup you can pour everything into) but be mindful that you don’t lose yourself along the way.

Being yourself and taking time for yourself doesn’t make you worse at your job, it actually makes you far better at what you do and more attractive to the people you want to work with.

So consider this your reminder:

Get the massage, book the tee time (or the simulator when there’s 2 ft of snow on the ground!), plan the weekend away with your partner.

Life isn’t something that starts “after this role” or “after the next win.”

It’s happening now.

Don’t put it off.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

Let people help you.

I know it’s hard.

Hard to admit you’re not the macho man/woman who can handle it all on your own.

But you can’t do it all yourself.

Nor should you.

Let people help you.

It’s going to feel scary.

But you’ll be met with overwhelming support.

Whatever you’re working on - let people help.

That’s it.

Have a great weekend!

If you aren't featuring AI in your startup job search, this is a wake-up call.

Block just laid off ~50% of its staff, citing AI as the main reason.

Also this week, Meta announced they're re-interviewing all their PM's with a Product Sense with AI interview with the risk of those who don't perform well potentially being marked as "legacy PM" vs "AI PM".

(You can read more about the Meta interviews in Ben Erez' post here https://lnkd.in/e2KuUPcP)

𝗜𝗳 𝘆𝗼𝘂'𝗿𝗲 𝗶𝗻 𝗮 𝗷𝗼𝗯 𝘁𝗼𝗱𝗮𝘆 𝗵𝗲𝗿𝗲'𝘀 𝘄𝗵𝗮𝘁 𝗜'𝗱 𝗱𝗼:

1. See if your company will sponsor you to take a course on how to use Claude Code, Devin, agent orchestration/workflows, whatever is most applicable.
   
   Our team is currently taking Sara Davison and Tyler Fisk's Maven course called How to Scale A Business With AI & Agentic Workflows - Foundations.
   
2. See if your company will sponsor you to join communities of people building with AI.

Get around others, see what they're building and how they're implementing AI in their day-to-day

3. Start a club inside the company that meets regularly and shares AI workflows, tips, tools, and tactics.

𝗜𝗳 𝘆𝗼𝘂'𝗿𝗲 𝗻𝗼𝘁 𝗶𝗻 𝗮 𝗷𝗼𝗯 𝘁𝗼𝗱𝗮𝘆, 𝗼𝗿 𝗶𝗳 𝘆𝗼𝘂𝗿 𝗰𝗼𝗺𝗽𝗮𝗻𝘆 𝘄𝗼𝗻'𝘁 𝘀𝗽𝗼𝗻𝘀𝗼𝗿 𝗵𝗲𝗿𝗲'𝘀 𝘄𝗵𝗮𝘁 𝗜 𝗿𝗲𝗰𝗼𝗺𝗺𝗲𝗻𝗱 𝗱𝗼𝗶𝗻𝗴:
 
1. If you're self directed, jump into the AI YouTube sphere and start walking through tutorials while using LLMs to act as your tutor.
    
2. If it's harder for you to get started or keep accountable to testing and experimenting, consider investing in yourself and taking a course or joining a community like the one above.

Do you need to be an absolute AI savage in your startup job search? 

𝗜𝘁 𝘄𝗼𝘂𝗹𝗱 𝗵𝗲𝗹𝗽 𝗯𝘂𝘁 𝘆𝗼𝘂 𝗱𝗼𝗻'𝘁 𝗮𝗯𝘀𝗼𝗹𝘂𝘁𝗲𝗹𝘆 𝗻𝗲𝗲𝗱 𝘁𝗵𝗮𝘁.

Will it significantly help your candidacy if you can proactively show the team what you can implement inside their business leveraging AI in your function and that you're AI literate?

𝟭𝟬𝟬% 𝘆𝗲𝘀. 

This isn't meant to scare you.

It's to show you a potential advantage you can gain by using these tools and workflows today and showing them off to the teams you're interested to join.

Start tinkering.

Start testing.

Start building.

Proactively share your work before, during, and after your interview process.

---

🔔 Follow me, Kyle Thomas for more startup job search advice.
♻️ Repost to help others land their dream job!

If you only had one hour this week to work on your job search, this is where it should go 👇

(And it’s not generic advice of applying, tweaking your résumé, or sending another batch of outreach. Thank God.)

Every week I talk to ambitious operators asking the same question: 

"How much time should I actually be spending on this?"

Most job searches feel like a full-time job because people skip the foundational step: they never define what they're actually aiming for.

Instead, they burn hours: 

→ Applying to roles they're only half excited about

→ Sending vague outreach that goes nowhere

→ Rewriting their résumé for the third time this month

𝗜𝗳 𝘆𝗼𝘂 𝘀𝗽𝗲𝗻𝗱 𝗼𝗻𝗲 𝗳𝗼𝗰𝘂𝘀𝗲𝗱 𝗵𝗼𝘂𝗿 𝗱𝗲𝗳𝗶𝗻𝗶𝗻𝗴 𝘆𝗼𝘂𝗿 𝗶𝗱𝗲𝗮𝗹 𝗿𝗼𝗹𝗲 - 𝗯𝗲𝗳𝗼𝗿𝗲 𝘆𝗼𝘂 𝗮𝗽𝗽𝗹𝘆 𝘁𝗼 𝗮𝗻𝘆𝘁𝗵𝗶𝗻𝗴 - 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵 𝘄𝗶𝗹𝗹 𝗰𝗵𝗮𝗻𝗴𝗲. 

Here's how:

𝟭𝟱 𝗺𝗶𝗻𝘂𝘁𝗲𝘀 → 𝗗𝗲𝗳𝗶𝗻𝗲 𝘁𝗵𝗲 𝗰𝗼𝗺𝗽𝗮𝗻𝘆

Write down the environment you want: stage, industry, pace, culture, mission you care about. This is your filter that everything flows through. 

Here's the kicker that most people skip: write down WHY that's the place for you.

You want to find the thing you're pulled towards, not just what everyone says is "hot right now".

𝟮𝟱 𝗺𝗶𝗻𝘂𝘁𝗲𝘀 → 𝗗𝗲𝗳𝗶𝗻𝗲 𝘆𝗼𝘂𝗿 𝘃𝗮𝗹𝘂𝗲

Get specific about problems you solve:

→ What have you solved that's relevant to this stage?

→ What would you own in this role?

→ What outcomes would you drive in 6-12 months?

Be quantifiable.

𝟭𝟬 𝗺𝗶𝗻𝘂𝘁𝗲𝘀 → 𝗠𝗮𝗸𝗲 𝗶𝘁 𝘁𝗮𝗻𝗴𝗶𝗯𝗹𝗲

List the day-to-day tasks someone in this role would do.

This turns a fuzzy concept into something you can pitch.

𝟭𝟬 𝗺𝗶𝗻𝘂𝘁𝗲𝘀 → 𝗣𝗿𝗲𝘀𝘀𝘂𝗿𝗲 𝘁𝗲𝘀𝘁 𝗶𝘁

→ Who's the internal buyer?

→ What pain are they feeling?

→ Can you name 5 companies that need this today?

𝗘𝘅𝗮𝗺𝗽𝗹𝗲 𝗼𝗳 𝗮 𝗜𝗱𝗲𝗮𝗹 𝗥𝗼𝗹𝗲: 𝗛𝗲𝗮𝗱 𝗼𝗳 𝗘𝗻𝗮𝗯𝗹𝗲𝗺𝗲𝗻𝘁 𝗮𝘁 𝗦𝗲𝗿𝗶𝗲𝘀 𝗕 𝗦𝗮𝗮𝗦

Company: Fast-growing B2B SaaS, post-PMF, 50-200 employees

Problem: Sales scaling faster than systems - inconsistent ramp, plateauing win rates

My value: Build enablement that shortens ramp and improves close rates

Outcomes: Reduce time-to-quota 30%, improve win rates 10-15%

Buyer: CRO feeling pain of inconsistent execution as headcount doubles

𝗕𝘆 𝘁𝗮𝗸𝗶𝗻𝗴 𝘁𝗵𝗶𝘀 𝗵𝗼𝘂𝗿: 

𝗬𝗼𝘂𝗿 𝗼𝘂𝘁𝗿𝗲𝗮𝗰𝗵 𝗯𝗲𝗰𝗼𝗺𝗲𝘀 𝘀𝗽𝗲𝗰𝗶𝗳𝗶𝗰.
Not "Are you hiring?" but "I saw your team doubled - are you feeling pressure on ramp time? I've solved this at [Company X]."

𝗬𝗼𝘂𝗿 𝗮𝗽𝗽𝗹𝗶𝗰𝗮𝘁𝗶𝗼𝗻𝘀 𝘀𝘁𝗮𝗻𝗱 𝗼𝘂𝘁.
You're addressing their exact pain with proof you've solved it.

𝗬𝗼𝘂𝗿 𝗶𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄𝘀 𝗮𝗿𝗲 𝘀𝗵𝗮𝗿𝗽𝗲𝗿.
You know the problem, buyer, and outcome. You're not guessing.

𝗬𝗼𝘂𝗿 𝗻𝗲𝘁𝘄𝗼𝗿𝗸 𝗸𝗻𝗼𝘄𝘀 𝗵𝗼𝘄 𝘁𝗼 𝗵𝗲𝗹𝗽.
You have a crisp answer that makes them think of specific companies.

One focused hour upfront saves weeks of scattered applications.

Getting hired at a top startup isn't about your resume.
It's how you make the hiring team feel.

Top performers don't just apply. They make the hiring team think:
"Wow, this person already feels like part of the team!"

To do that, they go all-in on their:
→ Networking outreach
→ Applications
→ Interview prep

Here's what that looks like...

1️⃣ 𝐃𝐞𝐞𝐩 𝐫𝐞𝐬𝐞𝐚𝐫𝐜𝐡 𝐢𝐧𝐭𝐨 𝐭𝐡𝐞 𝐜𝐨𝐦𝐩𝐚𝐧𝐲 𝐚𝐧𝐝 𝐢𝐭𝐬 𝐩𝐞𝐨𝐩𝐥𝐞.
↳ They consume all the interviews with the founders.
↳ They know the founding story
↳ They know the language they use
↳ They know what the team cares about
↳ They know the priorities of the company
↳ They know how they talk about their customers

They research each interviewer like a podcaster.
↳ They know the jobs they have had
↳ They know where they went to school
↳ They've found similarities in their backgrounds
↳ They know how long they've been at the company
↳ They know how this role will impact each interviewer

The more they research the easier it is to turn the interview into a conversation.

2️⃣ 𝐈𝐧-𝐝𝐞𝐩𝐭𝐡 𝐩𝐫𝐚𝐜𝐭𝐢𝐜𝐞 𝐟𝐨𝐫 𝐞𝐚𝐜𝐡 𝐢𝐧𝐭𝐞𝐫𝐯𝐢𝐞𝐰 𝐬𝐭𝐚𝐠𝐞.

They don't just wing it in the interview.
↳ They craft answers and rehearse them out loud
↳ They proactively identify hiring manager doubts
↳ They identify ways to proactively remove doubts
↳ They do mock interviews with friends or coaches
↳ They use AI to come up with questions to practice

They want to go through as many simulations of the game as possible before they're put on the field.

Live practice with feedback trumps all other practice.

3️⃣ 𝐃𝐞𝐥𝐢𝐯𝐞𝐫𝐢𝐧𝐠 𝐯𝐚𝐥𝐮𝐞 𝐛𝐞𝐟𝐨𝐫𝐞, 𝐝𝐮𝐫𝐢𝐧𝐠, 𝐚𝐧𝐝 𝐚𝐟𝐭𝐞𝐫 𝐢𝐧𝐭𝐞𝐫𝐯𝐢𝐞𝐰𝐬.

They proactively identify creative ways to showcase
↳ Skills
↳ Network
↳ Experience
↳ Ability to drive impact
↳ Interest and excitement in the company

They do this by sending value deliverables like:
↳ Personal pitch decks
↳ 30-60-90 day plans
↳ Case studies
↳ Connections
↳ Playbooks

They compete on generosity and try to deliver as much value as possible to demonstrate their abilities.

4️⃣ 𝐆𝐨𝐢𝐧𝐠 𝐚𝐛𝐨𝐯𝐞 𝐚𝐧𝐝 𝐛𝐞𝐲𝐨𝐧𝐝 𝐰𝐢𝐭𝐡 𝐨𝐮𝐭𝐫𝐞𝐚𝐜𝐡 𝐚𝐧𝐝 𝐟𝐨𝐥𝐥𝐨𝐰-𝐮𝐩.

Everyone sends thank you emails (hopefully).

Almost no one sends…
↳ Testimonial videos from your network
↳ Thank you videos
↳ Follow up value

Things like that are little ways to stand out to the team.

"But won't it look like I'm desperate or trying too hard?"

𝗡𝗼, 𝘁𝗵𝗲𝘆 𝗹𝗼𝘃𝗲 𝗶𝘁.
Founders love it
Recruiters love it
Hiring managers love it

It won't only help you land the job.

It'll help you earn instant credibility and attention.

Want to stand out?
It's not about doing what's 𝗿𝗲𝗾𝘂𝗶𝗿𝗲𝗱.
It's about doing what's 𝘂𝗻𝗲𝘅𝗽𝗲𝗰𝘁𝗲𝗱.

What’s the most “over-the-top” thing you’ve done in an application or interview?
Drop your story in the comments 👇

---

🔔 Follow me, Kyle Thomas for more startup job search advice.
♻️ Repost to help others find their dream job!

Cold outreach is dead.

Or so one of the members of my community thought.

But then he landed an interview for his next startup role.

Here’s how he did it, so you can do it too 👇

He left this message in the Early Accelerator:

"𝘕𝘦𝘷𝘦𝘳 𝘪𝘯 𝘢 𝘮𝘪𝘭𝘭𝘪𝘰𝘯 𝘺𝘦𝘢𝘳𝘴 𝘥𝘪𝘥 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘐 𝘸𝘰𝘶𝘭𝘥 𝘣𝘦 𝘢𝘣𝘭𝘦 𝘵𝘰 𝘴𝘶𝘤𝘤𝘦𝘴𝘴𝘧𝘶𝘭𝘭𝘺 𝘦𝘹𝘦𝘤𝘶𝘵𝘦 𝘤𝘰𝘭𝘥 𝘰𝘶𝘵𝘳𝘦𝘢𝘤𝘩. 𝘏𝘰𝘸𝘦𝘷𝘦𝘳, 𝘴𝘦𝘦𝘪𝘯𝘨 𝘵𝘩𝘦 𝘦𝘹𝘢𝘮𝘱𝘭𝘦𝘴 𝘩𝘦𝘳𝘦 𝘢𝘯𝘥 𝘨𝘰𝘪𝘯𝘨 𝘵𝘩𝘳𝘰𝘶𝘨𝘩 𝘵𝘩𝘦 𝘮𝘰𝘥𝘶𝘭𝘦𝘴 𝘨𝘢𝘷𝘦 𝘮𝘦 𝘵𝘩𝘦 𝘤𝘰𝘯𝘧𝘪𝘥𝘦𝘯𝘤𝘦 𝘢𝘯𝘥 𝘵𝘰𝘰𝘭𝘴 𝘵𝘰 𝘥𝘰 𝘪𝘵!”

𝗪𝗵𝗮𝘁 𝗳𝗹𝗶𝗽𝗽𝗲𝗱 𝘁𝗵𝗲 𝘀𝗰𝗿𝗶𝗽𝘁?

→ Plug-and-play templates

→ Killer examples from past and current members

→ A confidence reset from seeing others doing it

𝗔𝗻𝗱 𝗵𝗲𝗿𝗲'𝘀 𝘁𝗵𝗲 𝗲𝘅𝗮𝗰𝘁 𝗲𝗺𝗮𝗶𝗹 𝘁𝗵𝗮𝘁 𝗼𝗽𝗲𝗻𝗲𝗱 𝘁𝗵𝗲 𝗱𝗼𝗼𝗿 👇

Hi Tom,
I wanted to follow up on my candidacy for this position.
In case it is helpful, I've also attached a case study detailing a project I worked on at a previous company.

The presentation shows:
1. How I rapidly identified the problem
2. Implemented a new data tracking system to analyze the information
3. Came up with a novel solution that led to real business results

If this is the kind of work you are interested in, let's connect.
Thanks,
Steve

𝗧𝗵𝗮𝘁'𝘀 𝗶𝘁!

Simple, confident, straight to the point (with a clean case-study deck attached).

You can do everything “right” in a startup job search, and still get nowhere.

So what if the answer is doing the thing that feels wrong?

Let’s turn the clock back to 2012.

I was stuck in a cubicle in data entry hell. 

So… I updated my resume and did the “right” thing.

I applied to dozens of jobs.

Many of them were startups.

What were my results?… You guessed it!

Nothing. Nada. Zilch.

Then I quit my job and moved to NYC with 90 days of savings and zero network.

Not what many would recommend as the “right” strategy.

But I threw out the old playbook:
→ Stopped focusing on roles and started focusing on people

→ Allowed myself to go down interest driven rabbit holes

→ Offered to do free or low paid work to get my foot in the door

→ Did something for myself every single day

It felt uncomfortable to not to be applying to dozens of roles each week.

But it also felt much more aligned with why I was making the change in the first place.

In 90 days, and with some luck (preparedness + opportunity), I was employee #250 at Uber.

I see this everyday in the startup job seekers we coach inside Early.

Those who are successful do the things that feel 𝘸𝘳𝘰𝘯𝘨 to most candidates:

 • They focus on clarity before taking massive action
 • They build their confidence and resources before outreach and application
 • They have a “yes and” approach combining warm and cold outreach to leave no stone unturned (and they do lots of it)
 • They do everything in their power to stand out instead of fit in
 • They combine high quality with increasing amounts of quantity
 • They’re follow up hounds, persistent but polite of course
 • They do whatever it takes to get in the right room or in the right city

To many of them, this feels uncomfortable, “out of character”, or just flat out “wrong”, but it’s what gets noticed. 

Especially at startups.

Stop worrying about what the outside world will think of what you’re doing.

Stop worrying if this is the “wrong” way to go about the job search.

I’ve found that often the thing that feels “wrong” is just the discomfort of doing things you’re not good at yet or putting yourself in positions that will stretch you.

You 𝗻𝗲𝗲𝗱 to tap into your unfair advantages more.

The number one question I get asked is: “How do I network more effectively?”

Most people assume the answer is better cold messages...

It’s not.

The real answer is when and why people reach out.

𝗠𝗼𝘀𝘁 𝗼𝗽𝗲𝗿𝗮𝘁𝗼𝗿𝘀 𝗼𝗻𝗹𝘆 𝗺𝗲𝘀𝘀𝗮𝗴𝗲 𝘄𝗵𝗲𝗻 𝘁𝗵𝗲𝘆 𝗻𝗲𝗲𝗱 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴: a job, a referral, an intro.

That instantly creates friction because the message feels transactional.

When I ask, “How much networking are you doing?” these are the people who answer…

“I’ve been messaging people I’m connected to at companies with open roles but I don’t feel like it’s getting me anywhere.”

Should you be doing that? Of course.

Should those be the only messages you’re sending? Absolutely not.

You unfair advantage can come from many places. Here are just a few:

 • Your background
 • Your interests
 • Your location
 • Your network
 • Your communities
 • What you’re learning
 • What you’re building

Here’s how to reframe your thinking when it comes to networking:

Effective networking is about timing, shared context, clearly demonstrated genuine interest, and mutual value… not just writing better cold outreach.

Here’s an example of how I started dozens of conversations with tremendous operators:

I recently started an agentic AI course alongside ~50 other people.

Instead of waiting until I needed something, I reached out while we were all in it together.

I WAS introducing myself and starting a conversation to build the early stages of a relationship.

I WASN’T asking for anything.

The course acted as the perfect context to narrow the credibility and familiarity gap, and because of that, the messages felt natural.

Within a matter of a few days I added over 50 top operators building with AI to my network.

That’s the framework to steal:

→ Don’t start from zero.

→ Borrow credibility from the environments you’re already in.

→ Think courses, cohorts, events, communities, interests.

→ If you’re not part of one, what could you join? What door could you unlock?

→ Even shared interests or conversations can achieve the same thing - spend time in people’s feeds and see what they’re posting about. Research their LinkedIn profile and see where they’ve been. What is it you can learn from them? What value could you provide to them?

When the context and genuine interest does the heavy lifting, the relationship starts easier, faster, and with less friction.

That’s how networking stops feeling awkward.

📌 Save this post to come back to it later. 

✉️ Looking for a new startup role? DM me and we’ll support you in your search.

You ended the interview with "I'm really excited about this role."
They ended it with a 6-month ramp plan in the hiring manager's inbox 📥

Umer landed a VP-level Strategy & Operations role at an AI company without any prior AI experience.

And this was just 𝐨𝐧𝐞 of the 3 Series A-E offers he landed in 90 days.

Here's what made him stand out:

𝟏. 𝗟𝗼𝗼𝗺 𝘃𝗶𝗱𝗲𝗼𝘀 𝗮𝘁 𝗲𝘃𝗲𝗿𝘆 𝘀𝘁𝗮𝗴𝗲

Instead of generic cover letters, he sent personalized Loom videos to recruiters and team members after applying.

After each interview, he followed up with a 1-3 min video within 30 min, expanding on something discussed in the call.

𝟐. 𝗔 𝗽𝗼𝘀𝘁-𝗳𝗶𝗻𝗮𝗹 𝗶𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄 𝗱𝗲𝗰𝗸 𝗽𝗿𝗼𝘃𝗶𝗻𝗴 𝗵𝗲 𝘂𝗻𝗱𝗲𝗿𝘀𝘁𝗼𝗼𝗱 𝘁𝗵𝗲 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀

Most candidates say, "I'm excited about this role" and leave it at that.

Umer created a comprehensive presentation that included:
a) A 6-month ramp-up plan 
b) Mapping of his skills to their immediate opportunities
c) His understanding of key stakeholder teams and their priorities

This directly addressed his lack of industry experience by showing he could embed himself quickly.

𝟑. 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰 𝗿𝗲𝗳𝗲𝗿𝗲𝗻𝗰𝗲𝘀 𝘁𝗶𝗲𝐝 𝘁𝗼 𝘁𝗵𝗲 𝗶𝗻𝘁𝗲𝗿𝘃𝗶𝗲𝘄 𝗽𝗮𝗻𝗲𝗹

When it came time to share names of references, Umer chose his carefully.

For the AI role, one reference was from a previous manager who had made the same logistics-to-AI ops jump he was attempting.

𝗧𝗵𝗲 𝗼𝗳𝗳𝗲𝗿𝘀:

1. A Series C role (from LinkedIn + referrals)
2. A VP-level Series A role (from LinkedIn recruiter outreach)
3. A Strategy & Ops role at a Series E AI company (no JD posted, came directly from networking inside the Early Accelerator community)

Each was attractive and required different tradeoffs.

𝗜𝗻𝘁𝗲𝗿𝗲𝘀𝘁𝗶𝗻𝗴𝗹𝘆, 𝘁𝗵𝗲 𝘄𝗶𝗻𝗻𝗶𝗻𝗴 𝗿𝗼𝗹𝗲 𝘄𝗮𝘀𝗻'𝘁 𝘁𝗵𝗲 𝗯𝗶𝗴𝗴𝗲𝘀𝘁 𝘁𝗶𝘁𝗹𝗲 𝗼𝗿 𝗵𝗶𝗴𝗵𝗲𝘀𝘁 𝗰𝗼𝗺𝗽.

It was the one with:
→Clear scope to grow
→A manager he trusted
→A well-funded, fast-moving market
→100% industry alignment (working at the edge of AI)

𝗛𝗼𝘄 𝗵𝗲 𝗴𝗼𝘁 𝘁𝗵𝗲 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝘁𝗼 𝗲𝘅𝗲𝗰𝘂𝘁𝗲 𝘁𝗵𝗶𝘀:

Before joining Early, his search was scattered. He knew what he wanted (remote-first, stability, a pivot from logistics), but his value prop was unclear, and interesting leadership roles felt out of reach.

𝗪𝗵𝗲𝗻 𝗵𝗲 𝗷𝗼𝗶𝗻𝗲𝗱 𝗘𝗮𝗿𝗹𝘆:

→He eliminated guesswork: The program provided structure to define his role scope, company stage, and priorities upfront. That made decision-making easier.

→He leveraged the community: Access to like-minded operators sharing networks, referrals, and best practices led to a role that was never posted. 

→Depth beat volume: Better datasets and sharper company research meant fewer applications but higher signal conversations.

𝗧𝗵𝗲 𝗹𝗲𝘀𝘀𝗼𝗻: Being intentional from the start and being in the right environment beats just doing more.

You can find out more at beearly.com.

Stand out in startup job search

We’ve reached a strange point in hiring.

Operators are scared that sounding “too good” makes it look AI-written.

This came up in the comments on a recent post.

“I have an English degree. I’m not a grammar fiend, but I worry that if I send something too strong or too polished, someone will assume I used AI.”

That fear makes sense, and I’m seeing it everywhere.

Strong operators are second-guessing themselves and holding back because they don’t want to sound robotic.

The thing to remember is there’s a massive difference between AI-assisted thinking and AI-generated messaging.

AI-generated messaging:

 • Sounds smooth but familiar
 • Reads like it could’ve been sent to 50 companies
 • Says the “right” things without saying anything specific
 • Doesn’t have “soul”, “vibes”, opinions, or experiences

But AI-assisted thinking:

 • Helps to speed up research on a company/individual
 • Helps stress test your assumptions or approach
 • Helps to remove unnecessary fluff
 • Speeds you up without removing your voice

That’s why my reply to that comment was simple:

“Write like you talk.”

And… if you really want to remove all doubt, add a human layer AI can’t fake (at least not well).

Add a short 60-90 second Loom of yourself explaining why you’re excited about this company and talking through the impact you believe you can drive in the role.

In today’s world of AI bot mass application this human touch is rarely done, so it stands out immediately.

Operators, please remember: you don’t need to sound less capable to sound human.

Being human doesn’t mean being messy, vague or unprepared.

Human sounds like:

 • Polite but conversational
 • Sharing detailed lived examples
 • Clearly articulating interests and opinions
 • Conveying energy that’s specific to this company/person

Use AI to think more critically and move faster, but don’t outsource your judgment, your voice, or your curiosity.

The goal is to sound like YOU, and that’s exactly what hiring managers are listening for right now.

AI is great at ramping up your speed and volume (just look at the services saying they’ll apply to 50-100 jobs for you PER DAY).

But speed and volume don’t matter if YOU look and sound like THEM.

If you’re looking for more human advice like this, make sure to drop me a follow Kyle Thomas. 

I landed my role at early-Uber through all of the non-traditional job search methods, and now I help others identify what makes them unique so they can land dream startup roles.

“𝗚𝗘𝗧 𝗘𝗩𝗘𝗡 𝗖𝗟𝗘𝗔𝗥𝗘𝗥.” 

You should have this on a post-it on your desk.

Every week, I meet with operators who've been searching for months.

By this point, they’ve had dozens of conversations.

They have a polished resume.

And they seemingly have all the right experience.

Yet… they’re still stuck.

The harder the struggle, the more likely they've skipped the most important step: getting clear on what they actually want before doing anything else.

This is the part most job search advice skips entirely.

Don't just tell me where you're applying, tell me:
What role would you take if comp was equal across all of them?
Which companies would you join even if the title was one level lower?
What do you want to be known for in your next role?
Who do you want to be in 2 years and what kind of role will take you there?

You can't write a compelling outreach message until you can answer those.

You can't tell a great interview story until you know what chapter you're writing.

And you definitely can't negotiate well if you don't know what you're optimizing for.

After 100’s of conversations with incredible operators, I can tell you one thing.

𝗧𝗵𝗶𝘀 𝗶𝘀 𝘁𝗵𝗲 𝗺𝗼𝘀𝘁 𝗰𝗼𝗺𝗺𝗼𝗻𝗹𝘆 𝗮𝘃𝗼𝗶𝗱𝗲𝗱 𝘀𝘁𝗲𝗽. 

Not because people don’t know it’s important.

But because the internal work is harder than immediate actions like resume optimization and cold outreach tactics.

If you feel stuck on what to do next, please step away from the job boards and actually get clear on what you want. I promise you it’ll be worth your time.

What's one question you're currently wrestling with in your search? 

(My DM’s are always open if you want your search to stay private - otherwise comment below)👇

AI should speed up your job search… not make you sound like everyone else.

The TLDR here is this: don’t outsource your job search to AI.

I keep hearing it from hiring managers and recruiters at fast-moving startups, the pile all looks the same. 

It goes back to something our parents told us growing up - just because everyone else is doing it, doesn’t mean you should too 😅

And yes, recruiters are using AI too. I get it. But that's exactly the point. 

If both sides are outsourcing to the same tools, the person who shows up with genuine curiosity and a personalized message stands out above the rest. 

Here are some ways I’ve seen AI help:
→ Surfacing blind spots
→ Speeding up research
→ Automating manual work
→ Challenging your thinking
→ Aligning your examples with the JD

Here are some ways I’ve seen AI hurt:
→ Outsourcing your voice
→ Replacing your judgment
→ Mass apply, auto apply, & auto-fill

From what I can tell, there are two reasons people are doing this:

1. The quantity play - The job search is tough and after so many tailored applications someone can lose hope and turn to the shiny promises of mass application. It only takes one right? So why not apply to 50-100 jobs a day?

2. The perfection play - You don’t want to make a mistake and risk it landing you an opportunity so instead of being ok with the humanness of mistakes, trust the infallible robot.

The funny thing is, as AI has made looking good much easier to attain, it’s not the polish that stands out.

It’s the humanness.

When you fully outsource yourself to an LLM, AI starts to hurt your chances.

That’s because personalization is still the differentiator.

You can’t convincingly automate:
→ Why this company?
→ Why this role?
→ Why now?
→ Why you?

Genuine curiosity is hard to fake, and easy to spot when it’s missing.

So, how should you actually use AI in the job search?

Use it for:
→ Researching companies and markets
→ Turning raw, original thoughts into clearer structure
→ Pressure-testing your interview answers
→ Playing devil’s advocate
→ Speeding up iteration

AI should be your thinking partner, not your voice.

If your application reads like everyone else’s, you’ve removed the one thing that makes you valuable:

Your perspective. Your energy. Your enthusiasm. Your drive.

--- 

👋 Follow me, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

I keep seeing mixed advice and feelings on using AI in the job search. 

Where have you found it's helped you most? (Don't stress, your boss won't see you've voted!)

Where has AI helped you most in the startup job search? 

A few months ago, she was questioning her next move.

Today, she’s COO at a grassroots fundraising tech company. Here’s what changed.

𝗥𝗼𝗹𝗲 𝗹𝗮𝗻𝗱𝗲𝗱: COO 
𝗛𝗼𝘄 𝗹𝗼𝗻𝗴 𝘁𝗵𝗲 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵 𝘁𝗼𝗼𝗸: 88 days from joining Early. 
𝗪𝗵𝗮𝘁 𝗴𝗼𝘁 𝗵𝗲𝗿 𝘁𝗵𝗲 𝗿𝗼𝗹𝗲: Abundance mindset and authentic networking

She didn't land the role from a job board or blasting applications. The job came from a previous connection in her network.

But here’s how that actually took shape.

𝟭. 𝗦𝗵𝗲 𝗱𝗶𝗱𝗻’𝘁 𝘀𝘁𝗮𝗿𝘁 𝗯𝘆 𝗮𝘀𝗸𝗶𝗻𝗴, “𝗪𝗵𝗮𝘁 𝗰𝗼𝘂𝗹𝗱 𝗜 𝗱𝗼?”

She asked: 
→ What do I actually enjoy? 
→ Where do I thrive? 
→ What kind of environment do I want?

She realized she loved operations, just not 24/7 healthcare ops, and that nuance changed her approach.

From working with hundreds of startup job seekers I've seen that confidence doesn't come from some magical place or words of affirmation, it comes from creating a clear direction.

𝟮. 𝗧𝗵𝗲 𝗯𝗲𝘀𝘁 𝗿𝗼𝗹𝗲𝘀 𝗱𝗼𝗻’𝘁 𝗹𝗶𝘃𝗲 𝗼𝗻 𝗷𝗼𝗯 𝗯𝗼𝗮𝗿𝗱𝘀.

This role wasn’t broadly posted.

She heard about it from someone she’d connected with months earlier, after being clear about her interests, even when that first opportunity didn’t work out.

Networking isn’t about one ask, it’s about building familiarity over time. You don’t know which conversation will pay off - so treat them all like they matter.

𝟯. 𝗦𝗰𝗮𝗿𝗰𝗶𝘁𝘆 → 𝗔𝗯𝘂𝗻𝗱𝗮𝗻𝗰𝗲.

The biggest shift was mental.

Instead of chasing whatever felt “safe,” she got clear on what she wanted.

She came to realize:
→ She thrives in the details.
→ She loves operational efficiency.
→ She wanted to work outside healthcare.

When you move from scarcity (“I just need something”) to abundance (“I’m choosing the right fit”), your conversations and outcomes change.

𝟰. 𝗦𝗵𝗼𝘄𝗶𝗻𝗴 𝘃𝗮𝗹𝘂𝗲 > 𝗽𝗲𝗿𝗳𝗲𝗰𝘁 𝗮𝗻𝘀𝘄𝗲𝗿𝘀.

The hiring process was formal and hard to read. Many questions weren’t ones she had prepared for.

So she leaned into confident, honest responses.

Then, she recorded a Loom and built a 30/60/90 value document.

They’re using it now that she’s in the role.

Don't worry about having the perfect answers. Focus on putting your clear thinking and visible value on display.

That’s what we help people to do inside Early - find, prepare and land their dream roles.

The proof is in the pudding (or carousel in this case!)

Want to see similar job search success?

Apply to join the Early Accelerator at BeEarly.com

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